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Start and Scale Inside The Marketplace

Episode 33 Interview With Damon Brown

Missions and Marketplace Podcast

Episode 33

Interview with Damon Brown

Hello Everyone! I’m Priest Willis and this is Missions and Marketplace podcast episode number 33. Today I’m joined by Damon Brown. Damon Brown believes technology can bring us closer together and, after talking with him, you probably will, too. His recently acquired Apple Top 10 app, Cuddlr (now known as Spoonr), landed him on the cover of Wall Street Journal and kick started the platonic connection industry – really they were just hugs. His breakthrough TED Book “Our Virtual Shadow: Why We Are Obsessed with Documenting Our Lives Online” foreshadowed the modern analog living movement. His TED talks push the value of being fully present in our daily lives. His script-writing has empowered TED, Al Jazeera America and other outlets. Damon shares his entrepreneurial insights in his daily Inc. Magazine online column, Sane Success, and regularly contributes to Playboy, Entrepreneur and Slate.

You’ll notice that I especially had a great conversation with Damon because him and I spoke for over an hour and a half. And typically, when we talk that long I’ll break up the episodes but I wanted to leave it in its full state and let you hear it for yourself – something that you really can pull in as entrepreneurs and people listening to this podcast. I want you to really tune in on what Damon says. When Damon speaks, he is very thoughtful, he is very articulate. He is really intimate in his words, not only his writing, but in his words. He truly believes about empowering entrepreneurs with – as he points out in Inc. Magazine – Sane Success. You know, I wrote an article some time ago in the Feed Front Magazine about mentally breaking down your hustle. This is where people had been taught to “go after passion” until it almost breaks them and then finds this work/life balance. This in a sense almost creates anxiety. Damon is saying “look, I’m raising the family. I’m being at home and I’m doing it with some sanity in place. I want to make sure I put my priorities and legacy in place. I want to create things. I’m an entrepreneur like all of you guys. But I also want to do it with sanity in place.” And, I love it. I love the message of intimacy intact. And I hope you do too. Without further ado, here is my man, Damon Brown.

Welcome to Missions and Marketplace podcast. Join us as we talk to business and thought leaders to discuss their passion in and outside of business and how it drives them to give and be citizens of goodwill. Let’s get started.

PW: Damon welcome to the program.

DB: Thank you. thank you for having me.

PW: Yeah, I’m excited to have you. I’ve been looking forward to talking to you for some time now. You are probably one of the top people on my list that I’ve wanted to interview for so many different reasons – a lot of which we’ll discuss here in this podcast. Why don’t you tell the audience a little bit about yourself?

DB: I’m best known, or probably was best known, as a journalist. My background is journalism. I’ve two degrees and one of them from Northwestern. and I’ve spent several years as a journalist covering, in retrospect, the connection between technology and intimacy. And intimacy not in the traditional sense of, you know, people hooking up or dating. But intimacy as far as how technology connects us. How we can be in a long-distance relationship and technology can help with that. How when I laid the brick with my co-founder, my co-founders were in three different countries. and so…

PW: Wow!

DB: …we communicate. Yeah, I’ll get into that later but we’re communicating via technology. So, as I became a father, technology played a part into my connection to my kids. And so basically that ended being the pattern that I saw, at least in retrospect. So, I did that for many, many years – probably about 15, 16 years. I end up getting married and my wife had a fellowship up at Stanford and that brought us up to Silicon Valley. And when I was in Silicon Valley, I was writing right away for the New York Post and a lot of those guys. I was there in kind of the halcyon days when looking back at it coz I was there when iPhone launched. I was there when the iPad launched and I did a book on iPad then becoming a bestseller. I met Steve Jobs when I was there and I was actually there when he passed away, I was also at Silicon Valley that time. So, for those three – those three or four years I was there it was just, it was pop and then it was crazy. So, my colleagues and friends, we’d be eating ramen noodles and then, a year later then they became, on paper, they became millionaires or billionaires. And so, I end up hanging out with some of the first unicorns and they were just people that I was cool with. They say “Now man we’re cool”, whatever. And so, it was an amazing time to be there. What was interesting was that I was doing all this work. I was doing a lot of writing. We can get into it a little bit later but that journalism writing and newspapers and magazines lead to me writing books. I did my first major book which was called “Porn & Pong: How Grand Theft Auto, Tomb Raider and Other Sexy Games Changed Our Culture” and that had launched right as I was coming to Silicon Valley so the timing, I couldn’t have planned it better. I had a big launch party, really got connected with lot of folks there. Of course, with the connection, with the intimacy in technology. and I was doing all this stuff and I had no interest in getting involved in the start-up scene. And so, I had a lot of colleagues that are involved in start-ups but for me, I dabbled in a couple of things to have some conversation but it didn’t really great serious. Until I was actually talking with a friend of mine at the time and he was trying to remember a quote and he was like “I can’t remember this thing” and I said “well, isn’t there are app for that” and he said “no” and then I was like “okay. well then I need to create it”.

PW: [Chuckles]

DB: I mean it was as simple as that. It was very much a tipping point moment that lasted five minutes. And that got me into app development really quickly. And so, over the course of that period of time, probably about two or three years, I started developing an app which would later become So Quotable. And in developing the app, I started to research how we communicate even more. I actually did program way back in the day and we’re talking COBOL and the original C. [Laughs]

PW: Oh, yes. you’re going way back into COBOL…

DB: Yeah exactly. I love technology and so obviously, what I research. And so, I’ve been programming since I was four or five years old. But it’s one of those things where it was always like a hobby, and something that was fun, and I love systems so I just learn it for fun. And suddenly at that time I was in my 30s and I was pulling on all these stuff that I did in my past. And so, I had people that actually were going to help me out with the programming side and to be frank they flaked out on me. And so suddenly I was the man to get it together. And as that happened and the start-up thing got serious, I ended up proposing to my now wife. We moved down to Southern California to be closer to our respective families. and I’m originally from New Jersey but I have some relatives over here that I’m close to. And her families go over here in Southern California. So, we moved down here, left Silicon Valley, got a house within a couple of months after getting married – we had our first son coming. And so rapidly within like a year that was Silicon Valley, bought a house, got married, had a kid coming-our first one. And that was just insane. And this was happening the same time that the start-up is warming-up and my son comes out – which is one of the most beautiful moments of my life – and the people that were going to help out with the app disappeared. And at that same time, I had gotten a call to put the TED Conference and got really close to them – they’re a really, really great tight-knit community. And I end up connecting with the head of TED Books and we got along extremely well. I told him I was learning all this stuff about communication based on my research with So Quotable. I thought there might be a book there. And they said “alright let’s talk about it”. and suddenly I had a book deal with TED. And so, that ended being my second major book, “Our Virtual Shadow: Why, We Are Obsessed with Documenting Our Lives Online”. The most brief way I can explain it is that if you have Facebook, if you have Twitter, if you have Instagram in particular or even Snapchat; when you’re trying to capture particular moments that you care about, that’s going to pull you away from that very moment. The danger, the challenge with that, the irony of that I should say, is that using Snapchat or Twitter or Instagram, they’re not rich enough to capture the moment as well as you can by being present.

PW: Uh-huh. So true.

DB: And so… right? And so, I won’t go further into that. But yeah, I did a whole book on it. I’ll talk about it for a while. But I realized that by me working on So Quotable, I was contributing to that issue because if we’re having a great conversation and I want to capture a snippet of it as a quote and share with other people, I’m pulling myself out of the situation, I’m pulling myself out of our conversation. How do I deal with that? So, it ends up being all this research based on the app that in the end became my book with TED. And the book with TED came out before the app was supposed to come out. And in the book, I said the app was coming.

PW: [Laughs]

DB: So, let me put this into what they used to call seeing in a nutshell. So basically, I leave Silicon Valley, my colleagues and friends who were supposed to help out with the programming totally disappeared on me, I got my first kid, I’m the primary caretaker.

PW: When you say disappeared, what do you mean Damon? Did they just like “I’m not helping you” or did they just get back up in their own projects and disappeared?

DB: The person that was going to help the most had the equivalent of a midlife crisis…

PW: Okay.

DB: … and disappeared. Like yeah, and no one knew where they were.

PW: Got it. Okay.

DB: You know, they showed up later so they were fine but for that period of time they were not available.

PW: Okay. I thought this going to be the hater story. Like, “Dude I’m not going to help you succeed”. Okay.

DB: [Laughs] That would… You know, I would have preferred that.

PW: [Laughs]

DB: You know. People, you know people. If you deal with someone who’s a hater, then at least you know where they’re coming from.

PW: Very true!

DB: Right! But if it feels you had support from someone and they’re not really giving support, that’s harder.

PW: Uh-huh.

DB: That’ll be my thing just because I’ve experienced both as I’m sure you have. It just doesn’t make sense, right? So, the disappearing act. I got a book with TED. Like, you know, for me as a public speaker that’s like, you know, one of the – the Mount Everest. And it’s like I have a book with TED- major book, I’m on TV and do all that was appropriated to it, saying this app is coming and then I got a baby that I’m taking care of – no idea what I’m doing as a father, as most first time fathers don’t. My wife just went back to work so I’m completely on my own here trying to stay in my journalism business coz I’m still a journalist, you know. So, I was trying to support this book and the support that I had – technical support, coz I knew how to design, it but the technical support, the nuts and bolts parts of technology for this app So Quotable my first app – is gone. And so, I talk about that in my latest book, “The Bite-Sized Entrepreneur: 21 Ways to Ignite Your Passion & Pursue Your Side Hustle” where I kind of recount that story a little bit where it was many, many early mornings where I had my son Alec in my hand and I was programming with the other hand, and that was that. It ends up being this really intense hustle where I would get up at 3:15 in the morning and I know that my son woke up usually around 6:00, 6:15 and during the day I want to be fully present for him. There was a period of time where I tried to do both, where I tried to be the stay-at-home dad and take calls and work at the same time. And after a week or two of that, I realized it wasn’t going to work. It was slowly escalating to me waking up at like 5:00 but then I realize that I didn’t have time to shower. By the time I got into the groove, my son would be up etcetera. So, then it moves to 4:00 but then I didn’t have time to eat and then I couldn’t really function.

PW: [Laughs]

DB: And then 3:15, end up being my magic time. And so, the 3:15 thing lasted for several months. What ended up happening is that it’s funny what happens when you actually get focused – you have drive. Because within four months, I end up learning the Apple programing language which is called Cocoa Touch and that’s what we used to program for the iPhone and also the extension for the iPad. And so, and at learning that, I ended up designing the app.

PW: Did you learn that knowing that you were going to come in to like So Quotable and eventually Cuddlr and all of those other kinds of apps? Is that the purpose of you doing it? Or was it just you love the tech in going back to your earlier years of just trying something new and in getting into programming?

DB: It was the latter. Yeah, a100% the latter, like it was pure love. Like it was this – and it was also like a sense of completion too. Because again I’d promise through one of the, in my eyes one of the strongest organizations in America, I said yeah I’m going to do this. And so, it doesn’t matter if I have a 3-month old. It doesn’t matter if I’m exhausted. It doesn’t matter if, you know, some of my colleagues flaked on me. You know, my word is my bond so let me complete this. And I think I also do which is kind of – I recently read or it was on TV and it had an interview of what makes an entrepreneur. And I think it’s one of those things where you actually rise to those challenges. And when I look back at the times when I was at my very best, when I look back and say “oh, how did I do that? That’s amazing!”. It’s always those moments when things were the most challenging. Because that – you know, as it says, ” Fuel sharpens steel”. So, you have to have those challenges. You don’t make them coz some people make them. I don’t believe they should make them [Laughs] Life gives you enough challenges. but when life does give you these challenges, embrace them and say “okay, I’m going to go full force. I’m going to make this happen”. And so, within four months, I end up learning the Apple programming language, designed this thing, a couple of colleagues and friends that I could lean on they end up giving me good advice as far as with general methods, recommending some good programming books, looking in my code which was really, really helpful too but mostly, in the sense of getting me in the right mindset. And within that four-month period of time, I got a call from TED and they wanted me to speak.

PW: Wow!

DB: So, imagine if I didn’t put in that initial work. Coz remember I was doing all this. It was, I remember it was October of 2013, my son was three months and it was October and then it was just really, to be frank, like a dark, got-my-head-to-the-grindstone period from October to December. And then like after the first of the year, I got this call from TED. You know, coz I put my hat in the ring for doing a TED talk and then I was like, alright, well whatever.

PW: Okay.

DB: Not a chance of that. Right after the first of the year, about a month before TED was going to happen they sent me this email and they were like “Great! So, this is how you’ll get ready for your TED talk”. And I was like “What?” and then “Have I lost my mind?” and then suddenly I was finishing up the app and practicing the TED talk every morning.

PW: Wow! You know what’s amazing about your story, and just to take a step back here, is that you mentioned that all the while you were still a journalist. So, you were kind of dabbling into these other projects and doing other things that are love interests for you of course. I mean people wouldn’t spend the time necessarily that you would, if you didn’t love some of this stuff, just for fun that is. But what’s amazing is that you said you were a journalist. I listened to a video that you did, I believe you were talking to a group of journalists and you said you’ve spent 15, 16 years whatever it was creating your own business cards and you got to a point where you left the title journalist off.

DB: [Laughs] Right!

PW: Almost subconsciously agreeing with yourself if that makes sense that “I’m not just a journalist” which is what I used to identify myself with. You’ve stitched all these different things together as you were going along networking with different people. What I like is that your experience crosses many paths – from a writer, commentator on sex or intimacy to owning businesses, writer for world known magazines like Inc. How do you, I mean, you’ve kind of shared with us how you do it but where does that come from that you touched so many different things?

DB: I’ve talked about it a little bit in The Productive Bite-Sized Entrepreneur which is uh…

PW: … the new book

DB: … the book. It’s a new book, right. And that’s “24 Smart Secrets to Do More in Less Time” and one of the things I talked about is having a core.

PW: Uh-huh.

DB: So, I call it a mission statement or an elevator pitch is probably more accurate. I call them the elevator pitch but if you cut it in half; like something you can say really, really quickly and people will get it. Or if they don’t get it, they’ll see all your work and then they’ll understand. So, for me, it’s about how technology brings us closer. So, if you look at “Porn & Pong” which was about how sexuality and intimacy is depicted within video games and using video games as an analogy or representation of how technology has moved us forward in humanity. And then several years later, I did the book with TED “Our Virtual Shadow: Why, We Are Obsessed with Documenting Our Lives Online”, it’s obviously about social media and how that’s changing how we are connecting to each other for good and for ill. And if you look at, you know, the body of work before that, the15 or 16 years as a – just strictly as a journalist who focus on journalism then whether I’m writing for, you know I used to be a regular writer for Playboy. So, whether I’m writing for Playboy magazine, I used to write for Family Circle, I used to write for ARP Magazine. I used to write for Electronic Gaming monthly when they were around. If you read any of my material from any of those guys…

PW: And that’s the only reason why I read Playboy by the way. It was just for your articles.

DB: [Laughs]Just for my articles?

PW: No. Nothing else. Nothing else. [Laughs]

DB: [Laughs]. So, if you look at them, like the best example I can give was I was speaking at a journalism conference. I used to be on the Board of Directors of the American Society of Journalists and Authors. So, I was on there for a long time, it’s a great organization. I was really happy to volunteer with them. And I was at one of their conferences speaking, probably about a decade ago. And it was one of my proudest moments because I was telling them if they went on a newsstand right now, they could see my feature in Playboy and they could see my feature in Family Circle. And as a journalist that’s like, at least for me, that was such a huge point of pride to say that…

PW: … how diverse it is.

DB: Yeah how diverse. And not even from an ego standpoint but that was a moment where I was like “okay, I got this”. It’s not really about saying; which is what I was trying to get at when I did the keynote for the ASJ and the Society of Professional Journalists conference. That’s the, that’s what you, the video you had –

PW: That’s right.

DB: And anyone listening could catch that on DamonBrown.net, there’s a connection on there. But that’s what I was trying to get out when I did a keynote about a year ago, November 2015, was that we tend to get tied up in titles and we tend to say “okay, well I’m a print journalist. And so, if I have an opportunity to be on TV, I probably shouldn’t take it because all I want to do is write”. Or you can say “I’m an entrepreneur. So, if I have an opportunity to write a fantasy novel, I shouldn’t take it because that’s not my lane.” And you hear that a lot now, it’s like ” that’s my lane, that’s not my lane”. The things are that your lane shouldn’t be based on what your title is but should be based on what kind of impact you want to have on the world and what you want people to pay attention to.

PW: That’s so good Damon. That’s good stuff right there. That’s a quotable for this show for sure.

DB: [Laughs] Thank you. So, it’s about to develop, I call it, in the new book “The Productive Bite-Sized Entrepreneur”, I call it developing your core. And one of the things I talked about in that chapter is how people like Richard Branson and Oprah Winfrey, and folks like that and I’m connected to folks who work with them, they’re like amazingly productive. Especially Richard Branson, he brought in so many different things and the question is always how did they run all those things and still seem to be happy? And still seem to have a little bit of a life and they seem to be enjoying it? And the thing is, is that it’s not things that they run but what their focus actually is. I don’t know what Richard Branson’s focus is – only he knows that or perhaps he’s expressed it in his Losing My Virginity book that came out a few years ago. I don’t know what Oprah’s focus is. Only Gayle King and other folks know that and maybe she’s expressed them on her network. I know what my focus is and my focus is now two-fold; it’s showing how technology connects us and it’s also encouraging and inspiring others to pursue entrepreneurship within our current lifestyle. Those are my two things. that’s it. If I’m doing something outside of that, then that’s taking more energy than necessary and it’s also to a certain extent wasting my time because those aren’t my two core things. If you see an article of mine, if you see a tweet, if you see a video – it’s going to be connected to that. Even with the keynote at the ASJ-SPJ Conference, that was really about encouraging freelance journalists and authors to become more entrepreneurial. And so, that still fits within one of those two cores. So, I think that’s how – it took a while for me to understand that but I think that’s how I get everything done. When I was working on So Quotable and that was a total solo mission, my main thing was to show people how technology connects us and I love quotes, I love words, so that was my way of doing that and doing it from the side of an entrepreneur and not from the side of, say doing an article. And one of the things that I often talk about is the conversation I had with my friend about how hard it was to remember quotes. That conversation could’ve turned into a tweet that I send out and I said “hey I had this funny moment”. Or it could’ve become an article that I did for, say, Smithsonian Magazine about how it’s harder and harder to remember things because technology’s offloading everything. Or it could have become a book which to a certain extent I did with “Our Virtual Shadow”. But I looked at it and said, “you know what, this needs to exist. And if I didn’t do it, I don’t know if it’s going to happen. It’s something that I would use. I think it’s something that my colleagues and friends would use so let’s do it. Let’s make it happen.” And so, having that comfort level when you have your core set and you’re secure what your core is, you can go all over the place. If someone had the opportunity or find the idea for doing a movie right now, I might do it. But that movie would probably have to be connected to one of those two cores that I have and if I do that then it makes it easy. And I think that it makes it a lot easier to (1) market your stuff and (2) to gain trust in your audience or your readers or your customers. So, when Cuddlr came and I was one of the three co-founders, it was a natural fit because (1) I had the entrepreneurial background which So Quotable kind of set me up for and (2) it was about intimacy in technology. So, when people are like “oh you’re serious about this. You’re not just dabbling with So Quotable – it wasn’t a onetime thing. This is the second time”. At this point I’ve done 18 books, at that time I did about 14 books and half of them had to do with technology and intimacy. So, people look at the pedigree and say “oh! okay. He’s a co-founder in this but he’s been studying intimacy and technology for a decade and a half.”

PW: Uh-huh.

DB: It’s like “oh well maybe I’ll download this guy’s app and see what’s going on. Maybe he knows what he’s doing”. And so, there’s a certain level of respect that you get. But beyond the respect there’s a certain amount of courage and a certain amount of insight that you’re going to get if you decide to focus on one or two things.

PW: You blew up the whole system by moving from Silicon Valley, having all the connections that you had, when you started Cuddlr and still deciding to bootstrap the business. This is why I really admire what you do.

DB: [Laughs]

PW: Honestly. Because you are kind of really practicing and doing what you preach in a sense. I mean you are kind of owning your own destiny and again that’s another played out cheesy word – business word I know- but you are. Because you bootstrapped it and ultimately you guys were acquired. Let’s talk about Cuddlr. Walk me through what made you decide to bootstrap it versus going the VC route or using some of the connections that you established in Silicon Valley when you did.

DB: Sure. That’s a really good question. So, it was myself as co-founder, Charlie Williams and then there was also Jeff Kulak who was an initial co-founder and still was a co-founder but he ended up taking up a small role in it. So, it was really me and Charlie that were running the show during the process. There was a lot conversation we actually had with VCs and obviously, I was talking to my network like crazy – obviously. [Laughs].

PW: [Laughs]

DB: And I’m like “okay I’m doing this. What the heck am I doing?” For people, I was close says “What the heck am I doing? Should I run with this? Oh, my gosh, we’re on the cover of this newspaper. What am I supposed to do with this?” I’m not going to pretend that it was, that I knew exactly what to do. There was a lot of learning every single day but also, like you said the VC versus bootstrapping thing. We talked to quite a few VCs and there were some that approached us and I tell them that we’re just go on a network that we’re cool with. And there were two big, big reasons I think that we decided to do the bootstrapping route. First of all, there was nothing like Cuddlr. Along with my app, kind of not even as a compliment but I tend to have a pioneering spirit. Like if there’s something new to be done and a new way to do it then, if it fits my core then I’m going to go for it. That’s just my personality. It’s just, alright let’s take it to the next level. And so, what attracted us to creating Cuddlr was the same reason why VCs were being conservative with it. Because it was unique and so my big selling point for Cuddlr, coz my main, among other, duties, I’m probably considered the COO of Cuddlr and then also the CMO because I did the marketing for it. And as a COO, my main thing and the main vision, you might say, for it was that Facebook was about connecting with people you already know in a superficial way. And then Tinder, Grindr and all their ilk was about connecting with strangers in an extremely intimate way. And then, can we work with this gray area of connecting with people that you don’t know in an unsexual way. So, creating that intimacy, and Cuddlr, as the name implies was about connecting with people within your radius for a hug, for a cuddle. And it’s something, it was like this huge gray area and the more we started researching and getting involved in launching Cuddlr, the more excited I got. So, I realized there was this big space in there. And so, if you deal with this big gray space as a journalist, as a researcher, as an entrepreneur – all those things that I am now- you’re going to dive in and get really excited about it. If you’re a VC that’s investing, unless you have that same vision, you’re not going to quite get it. And so, that was, so finding VC, finding investment firms that understood the vision was difficult. What was funny about it is that they had to respect it because, I’ll get into the metrics a little bit, but our numbers for a little app are numbers that were pretty crazy. And so, there was a lot of conversations like “Wow! we don’t get it but you got a lot of users. Wait, we don’t understand”. And so there was a lot of explanation as far as with culture. To be frank, we kind of started that wave and it wasn’t until the waves started to crest out a little bit where those conversations started to heat up and by then we’re about to get acquired.

PW: Do you think your numbers took off right away because people initially maybe thought it was wholeheartedly a sexual nature. You know, they were kind of trained by Tinder and some of these other apps to kind of have a hook-up. So, you were genuine in the sense that you created this app for people to cuddle and just kind of create a human intimacy experience. But do you think somebody was going to bypass the system where it’d be like “yeah I know what they say this is, but it’s totally going to be a hookup”. Do you think that’s why the numbers were big to begin with?

DB: Maybe initially. sure. I’ll give some leeway to that but there were kind of two things that made it really intense. First of all, we are catering to an audience. Well let me start with the first, the other one. First of all, the amount of media attention we got was ridiculous. And so, we came out on September 18th, two years ago, we came out September 18th and by the next day we’re covered in Cosmopolitan, Glamour, Playboy, The Stranger which is a major newspaper up in Seattle. We’re on MTV news, all these things and quite…

PW: That’s unheard of unless you’re doing Pokémon.

DB: Seriously, yeah, it was similar to that type of vibe. And then by the evening we’re being talked about on the late-night shows. Like the real ones, you know, like the Jimmy Fallon level. And it’s like there’s a new app called Cuddlr blah blah blah, like totally part of the monologue but of course I lost my mind. I’m like, “what is going on here?’. The media attention was huge so that was a really big part of how we got so many users so quickly. I think another big part was that people were curious. And I’ll give you a little bit with that with people not sure what to make of it and I think that could be a huge advantage. And that was a really big thing where it’s like “this is something that’s totally different”. You know there’s a certain conservatism that’s in Silicon Valley. But then I can say this coz I lived there for a while and I have good friends that are up there so [Chuckles] they might not like me saying this but there’s a certain conservatism, there’s a certain monogamy where it would’ve been easier psychologically for us as founders to create a knock-off of Tinder and be like “okay it’s like Tinder but you go and eat something before you’d hook up”. You know it’ll be easy to like you know pave it a little bit and say “oh, you know, its Uber for dogs”. You know that kind of thing. [Laughs]

PW: [Laughs]

DB: Which actually isn’t a bad idea.

PW: [Laughs] I was just laughing off on the mike here coz I’m like you might be on to something actually.

DB: [Laughs] I could be a co-founder. [Laughs] No, but you know that kind of thing. And it was always, you know. Its 2016 now. If we flashback in 2014, its funny I’m just talking to you and I realized how much times have changed. In 2014 when the prevailing thought, when you talk to people at Silicon Valley particularly VCs, they’d say “well it’ll be a lot easier if you said it’s an Uber for foodies, it’s a Twitter for sociopaths”, you know. [Laughs]

PW: [Laughs]

DB: It’s what it’s at. Seriously if you do a Google, and I implore the listeners to do too, if you do a Google search on Uber for X whatever, you’ll find tons of articles from that period of time. So, that was a prevailing thought. Cuddlr required explanation and so it required a little bit of time and luckily to give myself credit for that, I think we marketed it really well. And so, we kind of have a good landing path for people. If they were curious about it, there was documentation online. What we did as far as the launch was, I had my connections in the journalism world coz I’ve been covering intimacy and technology and I reached out to some of the most trusted people in covering that. And I said “hey I’m doing an entrepreneurial thing now. I’m going to come out with this app. My co-founder actually came up with the idea and he’s the programming behind it. Let me know if you want to talk with him. so, I was very much hands-off and I’m like “hey, he’s my co-founder if you want to talk to him- cool”. And everybody was very enthusiastic and one person was like “yes, we want the exclusive on it”. And so, I end up setting up a Q & A. They had a great Q & A for Salon.com which was one of the major websites, news websites up at Silicon Valley. aAd so, we end up setting that up.

PW: Do you have people sign NDAs before you have these discussions with friends and stuff. I mean, coz it does seem it was really unique, it was in a different position.

DB: Oh, I see where you’re going. No actually. No, we didn’t. And I think that was part of the core thing and there’s like five different ways my brain is going, it was the reason behind that. But knowing the core of what you’re about (1) and if you know the core of what you’re about then even if someone tries to duplicate it, they really can’t. So, if someone else came out with Cuddlr, it would’ve been a different product even if they came out with the same service. So, what I mean by that is my co-founder, Jeff, he did the art for Cuddlr. And he has a particular artistic style that tends to be soft and inviting as opposed to artists who tend to have more aggressive, aggressive aesthetic. My co-founder Charlie, he actually was a part of the team with Shazam, the music app and he left them to do his own thing. And because he had moved out of the US to the UK, again he may have co-founder in different countries. And so, he moved to the UK and so his programming style worked really well because he got in the discipline to know how to pick up on things with sound and with location and stuff like that – all those things that Shazam is known for. And with myself, about the time the Cuddlr came out, I had already did 14 books and half of them were about intimacy and technology. And then I’ve written for a lot of the major publications. So, if someone else came out with Cuddlr, unless they have that team, it wouldn’t make much sense. And same with the marketing which is the part that I would take credit for where I could trust the people that I reached out to because I have built up relationships with them literally for, in some cases, for two decades. And so, I could go and say “hey, so and so, I’m working on this thing. Its super hush-hush. I’d be happy to give you an exclusive when we launch about a month from now”. And I trust them to not run with it because we have built up our relationship. But our relationship was based on me knowing my core. now, if I was doing an Uber then that would be a lot more difficult because I wouldn’t know who to trust, I wouldn’t know the subject and then people wouldn’t necessarily trust me, I wouldn’t have that depth. And I think that’s why really having one or two foci, coz it’s called foci, is really, really important. And so, no NDAs and we had no problems. It was cool. But also, I knew who to trust and who not to talk to but that all came from the previous experience. And that why it’s so crucial that people understand that they already have these unique skills that will make them a great entrepreneur. There’s few other entrepreneurs who have 20 years as a journalist, that’s my unique gift. You have a unique gift based on your life experiences and your experiences in your career before you start entrepreneurship. And so, there’s so many different ways that you can do it and there’s a certain beauty to that. And so, no NDAs, we knew how to get out to the press and end up getting really good feedback.

PW: You know I’m really impressed by this story. We’ll talk a little bit beyond Cuddlr here. For all the networks that you established with different people and you ultimately deciding to move from Silicon Valley, one of the first things that kind of stuck out to me was that; Silicon Valley, and I think there’s a lot of truth to this, for all its innovation, for all its creation, it is kind of conservative in the sense that they are looking for “okay, Uber was created. Show me the next Uber” versus you bringing a new product and something totally new and people are sometimes, not afraid, but they don’t know what to do with it. This is the difference and you talked about this too. You’ve done it on Inc and you’ve done different things like this and I want you to talk about this a little bit. But this is the difference between passion and persistence. Where you say that passion is the compass for you in a sense to kind of drive you to where you want to go but persistence ultimately will keep you pushing and keep you driving in spite of VCs saying “no this doesn’t make sense”, “I don’t know if I want to put my money in right now”. Talk about how the entrepreneurial community has gotten so wrapped up in passion and along the way they miss the persistence. And you know that’s the truth because people establish businesses and at the first meet they get a couple Nos from people they quit.

DB: Yes.

PW: They may not believe in it themselves necessarily so talk about why those two are so key and so different. And it’s okay that you have a child in the background coz this will make total sense coz you are the Bite-Sized Entrepreneur.

DB: [Laughs]. I was going to say I can hear either New Year right now or whatever. [Laughs]

PW: No. You know what? You know what’s funny? We’re going to keep that in because it only makes sense, I mean you’re in it, you’re in the flow, let’s do it.

DB: I’m living Bite-Sized Entrepreneurship right now so… [Laughs]

PW: [Laughs] You’re in the moment!

DB: I’m so glad you have four kids coz I don’t have to explain anything to you. That makes me feel a lot more secure.

PW: [Laughs] You don’t have to explain one thing. You don’t know how many times I’ve been in this situation and beyond Damon. It’s all good man, trust me.

DB: I have to give a shout out to my wife coz I’m so glad I’m not. I’ve been the primary caretaker and I’m so glad I’m not on my own. It’s nice to have 2 kids, it’s a wonderful thing.

PW: I have to agree. I mean if I’d been on interviews and talk about something, I always pick up my wife for the exact same reason. I mean, people always want to talk to me about business and “hey how did you do this”, at the end of the day and I’m being very honest with you coz you wanted to hear this I’m not blowing smoke. I wouldn’t be who I am without her in this realm.

DB: Wow!

PW: Yeah. It’s very, very true. I mean we’ve been together 20 years so she’s everything to me. Talk about the difference between passion and persistence.

DB: What’s funny is that if I do a quick step back, I realized that the muscle, I call persistence a muscle. So, the muscle of persistence goes way, way back for me. I’ve always been a freelance journalist; I’ve never been a staff writer. And so, that means that every day, as they say in the more harsh world, you eat what you kill. So, if I don’t work then there’s no money coming in and so that’s been the space that I’d been in for, again, almost two decades now. And so, it’s a matter when you’re a freelance writer, it’s a matter of sending pitches to different publications and initially don’t get any response. So, then you keep sending other pitches and then you get a “No” which is great coz then that means that you’re being acknowledged and then they might give a feedback on what’s wrong with it. And then you start getting yesses because now they know your name. And then based on that yes, that might give you a clip or some insight that gets you to a better publication, or get you to the next thing that you’re going to do. The book business is the same thing. For “Porn & Pong”, my first major book, I worked on it for five years and I was still on my twenties so five years is a really long time at that time. Not so much now. But at that time, it was a really long time. So, I spent five years on it, I went through two different agents. I had to fire one, all these other dramas and so forth. And I think I gotten, I want to say 47 rejections for it which is even a lot for the book industry. And then I finally got a yes and it end up being the perfect publisher for it. But it took five years of persistence and of course learning how to write well in the long form format and all that stuff. And so, what I’m saying is that I didn’t realize it but the previous professions that I’ve had were preparing me to get VCs saying “I have no idea what this app is about” or to have customers say or potential customers say “wow. No one’s going to use this app. That doesn’t make any sense”. And then of course eleven months later we get acquired. And a lot of apps do not get acquired, they just go away. And so, it’s like “oh! we were right”. But it takes trusting that vision and that’s where the persistence come from. People are passionate about stuff all the time. They might see a person going down the street and say “wow! they’re gorgeous! I’m really passionate about that person” and then they go back and then there’s nothing. You could be really into something that you’re eating and say “oh my gosh! I’m so passionate about this food” and the meal’s gone and whatever. You might have a hobby that you hear about or something that you hear about and that turns into a hobby. And you might do that hobby and be really excited about it for a few months and then it wanes. And I compare passion to love.

PW: Uh-huh

DB: Being in love with someone – that could go away or that could fade and then come back stronger in certain aspects. But the idea of having a commitment, of showing up every day, as Oprah and Brené Brown and other folks say, “When you show up every day, that’s something different”. To say that you’re really passionate about something, your friends are excited about it. Or when ideas sound amazing in your head but you haven’t done any work yet, that’s easy, that’s really easy. That’s like the nature of humanity. If there wasn’t passion, nothing would start. It’s like the spark but you need the wood, you need the gasoline, you need the charcoal, you need something to sustain it. Otherwise it’s just going to be a spark and when the wind blows the wrong way it’s gone. And people keep on mistaking passion for purpose and they’re two very different things. When I talk about me wanting to inspire people to find or create entrepreneurship within their current lifestyle, that’s a passion of mine but it’s also a purpose. And perhaps the purpose thing, the best way to describe it into persistence, maybe it’s about having something that’s beyond you and beyond your own desire. When I talk about showing people how technology could connect us, that’s something I’m really excited about and I love being a mouthpiece for it. But it really has to do with improving other people’s lives. You know when we were working on Cuddlr and the lifestyle that I was talking where I was waking up at 3:15 and work until 6:00, that apply to Cuddlr as well. You know my son had just turned one and then Cuddlr was out and then we were again on MTV and late night shows by the end of that week. It came out on a Thursday but it ended that week were all on late night shows, part of monologues and all that stuff.

PW: That’s insane!

DB: Yeah. a week later, my birthday is like in September, I remember it was on my birthday and exactly a week later we were number 1 in the App store and we had a 100,00+ users and 10,000 cuddles were completed. Insane! For a week! Three first-time entrepreneurs on three different continents just working together but the thing is that we had faith that this is, or at least particularly for me coz I was the culture guy, I had faith this is direction things were going to go. All that intensity had to be managed within my 15-hour a week schedule. and the only way I can get through that is if I was working towards something higher. And my two higher things were (1) having something that’s created a sense of pride and legacy for my child and not even from an ego standpoint like “Simba, this is your kingdom” type of thing….

PW: [Laughs]

DB: It wasn’t even that deep. But it was a sense of this is how you prioritize your life and if you’re really into something, you do what you have to do to make that happen and if you’re not really into something you’ll find every single excuse not to do it. And I can say that to my son, he’s well into toddlerhood now, so I can explain that to him and he’ll understand every word that I say. aAd he’s a fairly smart kid so probably reply me “yes dad. Okay”. But I don’t have to tell him that coz I was and I’m living that. And that is the biggest thing, I need to pass this on to him. This is what I believe in. This is how I lived my life so far in 30+ years, he needs to see this. And so, whether he decides to be a janitor at a high school or become the next Elon Musk – doesn’t matter. It’s the same thing, same principle, basic stuff. This a major key, this is a rule. There’s no way around that. Again, the passion versus persistence. That was number 1, that’s what got me up in the morning so I’d number 1 that. But (2) as the app moved forward, Charlie was initially in charge of communicating with the users coz those were usually technical issues. And then as we kind of grew into our roles and I got more responsibilities as co-founder, then I started taking on the user conversations. And were getting dozens, maybe a couple of hundred e-mails a day, I’m not exaggerating – every single day.

PW: Wow!

DB: Yeah. and I was like Gary Vaynerchuk or someone like that where I was like “okay were going to reply to everyone”. Seriously it’s like that were going to try to do this because it’s our brand and our responsibility is to facilitate intimacy. Again, we’re not Uber, were not Lift, we’re not Amazon, where they would keep you on hold or whatever. It’s like “no! our whole job is to connect people”.

PW: Good point.

DB: So, we got to connect with people and some talking people through stuff. People are, at least on e-mail, I’m pretty good with words, and in email it sounds like they’re in tears because our app suddenly crashed before they’re going to make a connection.

PW: Wow!

DB: Yeah. It’s just technology, it wasn’t even our app, that’s just what technology work. And I’m talking them through it. And also on my end there’s nothing I can do about it because those connections are based on location and so those if people have moved on, you don’t know who it was unless you happen to be in the same location again. So, there’s something transient about it too unless you make the connections and you could’ve saved that person’s name in your file. But anyway, every morning I’m getting these emails and if I sleep on that for an hour. If I say “you know what, I don’t want to do this today”, then there are people that are missing connections. Then the whole purpose of our app, and were saying were co-founders, the whole purpose of our app, were missing that. We’re missing our mission. That’s our mission, it’s to connect people. And if I’m not helping people connect and there’s an issue, and my names on it, that’s on me and that’s an awful way to be a co-founder.

PW: Uh-huh.

DB: So, there’s a high-level responsibility that I have and I think because I interviewed so many founders and spent so much time in Silicon Valley and I met founders who I believe truly cared about their customers and there’s some that just want it to IPO one day. And so, I knew what kind of founder I wanted to be. So, by that time, well into age and well into my time in the tech world, by the time I became a founder I took it very seriously because I knew what want to be or what I didn’t want to be. So, those two things, again my son and then responsibility to the public, those two things drove me. Those things create the persistence. Now was I passionate about the product? Definitely! Do I think it served a niche? A 100%! But that passion! When I’m up at 3:15 and I’m trying to calm down my kid who was screaming and I got 100 e-mails sitting there waiting for me and that would need a response. You know I got Wall Street journal calling for an interview and there’s other stuff. Passion is not going to sustain you! It’s going to go away. It’s going to be up and down. But persistence though, persistence and purpose those will hold you down and you need to know… I’m sorry I’m really going to get out for a minute.

PW: No please.

DB: Before you start anything, you really need to know why you’re doing it. Like you really need to know. As a society if we didn’t have our minds right, we’d jump into the sun. You know we’d launch with what we consider MVP, that was decent. Or we’d launch with a minimal viable product just to see if people or going to like it. We set up the media as well as we could and we only did Salon.com with exclusive interview and we had our own article that was on Medium.com. And Medium.com had just launched around that time. And so, we did it on that just because we wanted to express ourselves and explain what the app was before it came out. Those are only two media things we did. We’re all essentially first-time entrepreneurs coz So Quotable was a cult thing and it did really well within the TED community and the journalism community but it didn’t really blew up – which was fine. So, this was really my first serious entrepreneurial step. So, there was no reason to, and it was a strange app, so there was no reason to think well blow up. And it blew up! like huge! And then we end up having clones that were similar to Cuddlr that were coming out, we had people who were setting up like the equivalent of massage places but towards cuddles, and so there was a whole crop industry that came with that. Like all this stuff happened after we came out. By the end of the year, I mentioned the Wall Street Journal, we’re on the cover of the Wall Street Journal during the week of CS that January and they were talking about the cuddling industry. And we had started a lot of that. We had no idea that we are going to blow up. All I’m saying is that if we didn’t know what our purpose was, and we didn’t know how to be persistent and if it really matters, if we were just doing it just to do it, we would have imploded. No one could handle that kind of pressure and not have their core together. That’s what I talk about in the Bite-Sized Entrepreneur book series and what I, again with interviews like now and stuff like that, that’s one of the biggest things I talk to people about is, it doesn’t matter how much time you’ve spent with entrepreneurship; I got the app acquired, I spent 15 hours a week. So, it’s not about the amount of time. People get confused about that. They think that if I do 80 or 100 hours a week working on this app, working on this service, it’s going to succeed. Time does not equal quality time.

PW: Totally.

DB: Right? It’s about efficiency, it’s about focus, it’s about knowing what you’re doing. I had parameters like a family and other things that said, you can be really focused during this 15 hours. So, whatever your parameters are, think focus within those. It’s not about the amount of time, it’s not about following a trend and say “oh this is hot right now” coz nobody was talking about cuddling really when we came out. It’s not even the amount of that, it’s about knowing this higher purpose, knowing this focus, this thing that you maybe care about that you want to sacrifice your free time, if it’s a side hustle, your free time with. And once you have that established, then you have everything you need to move forward. But you could have a million dollars, you could have all the time in the world, you can have all this equipment but if you don’t have your purpose together, it’s just not going to work.

PW: Do you think people are losing the purpose and focus primarily because there is so much information out there. You know on the one hand, Damon, it’s great that we have so much information. People can learn how to design their own apps and create stuff even before they take any kind of class. You don’t necessarily have to go out to the library anymore like I used to and read…

DB: Yes.

PW: … Barnes and Noble and just soak up everything there. You could literally stay at home, sit in your room for 8 hours and learn how to do JavaScript relatively decent within twenty-four hours. But do you think there’s so much information is also killing people’s creativity because they are inundated and they think they have to run from one end to another? I mean, we went through a lot of your experience here and we’re going to get into the books and I think this is kind of leading into the Bite-Sized Entrepreneur and talking about the Bite-Sized Entrepreneur from a productive standpoint. But do you think with all the information out there and all the books people have to buy, all these other things that people have its just killing their sense of creativity? Because they have to feel like they have to be at every conference, they have to be in front of every caravan or talk and everybody else. What’s your take on just being in a noisy entrepreneurial world?

DB: I would actually split what you’re saying in two. I would say Yes and No. I would say things are too easy right now. So, it’s extremely easy to go on to wix.com and set-up a website for an app that you haven’t even thought that you might want to do. You’re thinking “well, I think I want to do this because this is the hot thing right now. Let me set up a website, let me do an e-mail, let me set a twitter account, let me go and do all these things. Let me go and learn JavaScript and go to Codecademy or something like that.” No disrespect to Codecademy, but go to those one of those guys, learn it within a week, knock it out. And then so you’re doing, in the Bite-Sized Entrepreneur, I have a chapter called Going Public. And it’s not about IPO’s but it’s about the danger of wanting the success or wanting the accolades which I think is even more dangerous, wanting the accolades, wanting the props, wanting to be part of the community when you haven’t paid your dues yet. When I say paying your dues, I don’t mean the 80-hour work-weeks or anything like that. I’m not talking about that. I’m talking about paying dues as far as having thought as far as what your purpose is. So, example I give back to my writing thing is that there’s some amazing writers out there or people who want to be writers. I will see them on Twitter and they will say “I’m working on my novel and I had a good day writing”. And it’s like “yeah I had another good day writing today” and then they’ll be sharing stuff about writing, and then they’ll share books that they read about writing. Absolutely no disrespect to them but the conversations that are happening are actually the time that’s being spent not writing. And so, it’s a matter of saying I want to talk about this stuff. I want to be part of this entrepreneurial community, I want to go to these conferences, I want to absorb all these things, I want to be part of the Silicon Valley scene but I haven’t done the work – that quiet time, that thoughtfulness to find out why exactly I want to be an entrepreneur or why exactly do I want to create this app. Why exactly am I sacrificing or want to sacrifice my time to do this? I haven’t thought about. I just want to be part of the scene. I want this feeling. I’ve a friend from way back in the day who wanted to be a concert pianist and this is back in college that I knew him so it must have been in exactly where he realized that he absolutely loves the piano but it was at a certain point where either he had to sacrifice everything to learn piano and to become one of the best or he had to let it go and just enjoy the concert. He decided to let it go, he went to a different direction, he’s totally happy now. But some of us never get to that point. Some of us actually don’t realize that we like the scene of it, the feel of it but we actually don’t want to create. And I think that’s the biggest challenge for people today is that there’s so many things that are enticing you to start creating when you haven’t really thought about what you will create. I know a lot of folks who want to go ahead and be an entrepreneur, be a consultant, but they don’t exactly know why. It just sounds good. So, I think that’s a danger is that the barriers to entry are so low right now. I can go ahead and I can hang out with you, decide that I want to get involved with something that I’m not involved with now. Throw up a website by the end of the day and then start handing out business cards. It’s so easy to get started. And like you said, I’m guessing were around the same age, so I’m a little bit of a different generation where when I started freelance writing, I had to go to the library. When I wanted to – my idea of publication when I first started twenty years ago was Smithsonian Magazine and I was living in Chicago at the time coz I’m at the Northwestern so I would go to my local library and I’d go through the last twelve issues of the Smithsonian. And that’s how I spent Saturday morning with. And then I’d write them a pitch and then I’d send it by email and that was a process. I’m not saying that process is better. What I am saying is that there were hundreds of other journalists who wanted to do the same thing that I wanted to do but they weren’t willing to put in the work to be there every Saturday morning. And so, that we did that right out. There are things that I really wanted to do but once I got into the heavy part of the process, I was like “No. I’m not going to do this”.

PW: [Laughs]

DB: [Laughs] “This isn’t me. No this isn’t me. there’s something else I can do.” And I’m happy to admit that because there needs to be some type of process; whether it’s an external process as far as the difficulty of getting a copy of Smithsonian Magazine coz they’re really expensive at that time or the difficulty of setting up a website which is why we have so many websites right now. You know, I’m really into hip-hop and as DJ Premier once said, we have a lot of popcorn rappers today. They’re like microwave, they pop out of nowhere and they go away just as fast.

PW: We definitely are from the same generation I know for sure coz I’m into hip hop and I know who DJ Premier is and I bet there’s not a lot of people that know who DJ Premier is. Well, not a lot of people who don’t know but the millennials let’s say, know DJ Premier.

DB: I would hope so, yeah. I wish we could spend like ten minutes talking about DJ Premier but I know we have more pressing stuff to talk about. [Laughs].

PW: [Laughs]Oh man! You know I could go with you round for round. You know one of the things I like, you have a quote out. I just want to cover your books just real briefly; so, you have the Bite-Sized Entrepreneur that’s out right now on Amazon, I highly suggest people go out check it out., you have the Productive Bite-Sized Entrepreneur which is coming our September 26 but it’s available for pre-sale, I highly suggest people check that out. I read it this week. I know people in high places so I got the book, I was able to read it. [Chuckles]

DB: [Laughs] Uh-oh, I got a leak, I got a leak!

PW: [Chuckles] It’s not going to leak! But one of the statements that you’ve made and this is where I want to kind of encourage these entrepreneurs coz people are looking for that area of saying “yes, how do I remain persistent and all that stuff”. You kind of hit it right on the head where it’s like sometimes you have to do what people don’t want to do to get what they got which is a big quote out there. But a quote that you said that I think is really, really good is “the belief that you have to sacrifice your livelihood to leave your entrepreneurial mark is a lie”. So, we talked about legacy, this is a very powerful quote to me that I read. I think you said on Inc or somewhere but I pulled it off your website. A lot of people of people do believe that they have to sacrifice their life because they think working a hundred hours a week is being productive. They think that they have this grandiose idea in their mind that if you want to be part of the community, as you were talking about, they have to give up everything and do all these other stuffs. You are the epitome of the Bite-Sized Entrepreneur so from a production standpoint, coz you have a family like I do, you are the person to write these books. I mean you’re in the middle of it. You created businesses; we talked about Cuddlr, we talked about So Quotable, we talked about all these other things that you’ve done. What are some things that you want us to pull from being the Productive Bite-Sized Entrepreneur? What are some key elements that you think an entrepreneur can take away from this podcast today and say “that made sense to me”? What are things that you’ve delved into the book that I may not have heard as an entrepreneur that I can take away today to say “you know, that’s what I need to work on for me to be more productive”?

DB: The theme, like you said, for the Bite-Sized Entrepreneur, the original one is that the belief that you have to sacrifice everything to make your entrepreneurial mark is a myth – it’s a lie. With the Productive Bite-Sized Entrepreneur, the second in the series, my main thing is productivity is a marathon or a cycle even, not a sprint. And you’re not going to be productive every day – those two things. So, in other words, when I tend to be an extremist, that’s another reason why I can write these books because I’ve been through both ends. I tend to be an extremist so when I get to be excited about an idea, my first instinct is to do all-nighters and to put everything else aside. Again, the passion part, I’m a passionate person so I’m ready to go in. And what I found in Silicon Valley and I talk about this particularly in the Bite-Sized Entrepreneur is again I had a colleague and friend who disappeared – totally burned out! Relatively young person too. And there are a lot of people like that because they believe that they have to be productive every single day. They have to crush it every single day. The human body doesn’t work like that. I don’t care if you’re 20 or 40 or 60 or 80, it doesn’t work like that. Your brain doesn’t work like that. Your will burn yourself out. Tt might take a month, it might take a day, it might take five years – it doesn’t matter. There’s going to be a certain point where you’ll going to be in the middle of an ocean, you have no idea where you are. It’s just the way it works.

PW: Uh-huh.

DB: And even the most successful entrepreneurs of our time, the Steve Jobs, he’s like a really highly recommended example. If you look in the course of his life, he had to come back to earth. So even genius like that, he had to come back to earth and say “wow! I need to reconnect with my estranged daughter! I need to actually have life balance. I’ve actually been a jerk to most people in the course of these 30 years. Maybe in need to calm down, maybe I’m wrong some of the time” – all these different things. So, if you look at him, an entrepreneur that most of us have looked up to for this generation at Silicon Valley, even he was like “I need to slow down”. So, it’s not a matter of saying “I’m going to stop” but a matter of saying “There’s this certain cycle to my productivity and I’m going to respect it”. In the Productive Bite-Sized Entrepreneur, I call the cycle of pursuing, doing, and renewing – so three steps. So, PURSUING is kind of that passion period where you’re really interested in looking into something. You want to see if something works. It’s like the pre-development stage whatever you’re into. So, you’re doing a lot of testing and seeing where things are going to go. The DOING part is when you’re actually in it – if you’re talking about an app, when you’re talking with the press the app is out, everything’s on fire, you’re moving everything, you’re just trying to keep up with what’s going on. And the RENEWING part which always happens is the quiet period where you go and you take in everything that you learned, everything you experienced and maybe pick up on some of the things that you missed as you were on the rollercoaster ride. And then it starts over again. And I found this from my own experience. I had the pre-launch period, the summer 2014 for Cuddlr that was our pursuing period. We’re like “okay, let’s test this idea or that idea. Let’s send out a little beta it to a few people that we trust. Let’s get some of the kinks out, you think this idea will work? Or maybe if we did it this way or that way, okay I think we got it”. And then obviously on launch day in September, then it was doing. And we stayed in that doing phase for what felt like forever. We had a popular app which was is definitely a double-edged sword. So, we were going and they what’s so funny is that Cuddlr got acquired at the end of July, beginning of August. And then things got really quiet for me – in a good way. And all of a sudden it was just me hanging out with my son and surely after that we found that we’re pregnant with the next one so I was enjoying that. And I was doing about the journalism again and I started my Inc column coz I talked with Inc and they’re really curious about my experiences with Cuddlr. So, the Inc column which is called the Sane Success, and that being essential to the genesis of the Bite-Sized Entrepreneur series coz I had no intention of doing these books. And I was working on this column doing it anywhere from one a week to several a week depending on how the flow was. And then feedback was so good and the thesis of the column was “Is it possible to be a passionate, strong entrepreneur without destroying your health or ruining your relationship?” – that was the thesis. And so almost every single column if you read it, and I have a few hundred on there now coz it’s been running for just over a year, if you go on to Inc. com and look me up there’s like almost all can fit into that theme. And as I started to work on those columns then, then that’s what where the Bite-Sized Entrepreneur series came from. I realized there was a pattern there and all those things. And so, working on that pursuing, doing and renewing end up being really helpful for me because there are lessons that I learned from that rollercoaster ride at Cuddlr that just hit me like in June, that hit me in May, like months after we got acquired and I had nothing else to do with Cuddlr. Suddenly, these things were dawning on me. And so, I think it’s important to have that space. One of the things that I talk about in the Bite-Sized Entrepreneur series is that it’s important to pause and re-evaluate what you’re doing and to stop to understand what exactly just happened. Because if you’ve been going non-stop for five years and you haven’t put any thought into where you are or where you want to go, then your mission, your business plan whatever you want to call it, is still based on what you believed five years ago, right? Cause you haven’t revised anything. You haven’t given yourself time to revise and so if you don’t give yourself time to revise anything then, its 2016, you’re thinking exactly how you were and having the same goals that you had in 2011 which is scary. And people do that all the time.

PW: That’s powerful.

DB: Its true! People do it all the time. They say “no I can’t afford to stop”, “no I got to keep doing”, “no, no I got to hassle every day, I can’t strategize right now”. But what’s the point of that? And so, my goals in 2011 were so narrow compared to where I am now. And not even a diss to my former self, just a lot’s changed in the five years.

PW: Uh-huh.

DB: And then in my life coz personally and professionally things have been awesome and crazy. But if I was going on my 2011 goals, I don’t know where I’d be. But the reason why I have these strategies, the reason why this book series is able to come out. Cuddlr didn’t exist five years ago, So Quotable didn’t exist five years ago, I didn’t call myself an entrepreneur five years ago. All these things just happened and with all that rapid development, as I look at it in the Silicon Valley, all that rapid development, the aberration that we say we love, if we follow the Lean Start-up Model with Eric Ries with Steve Blank, it really is about game and VPL, getting feedback and then revising it. Why would we be doing the same thing in our lives? Why wouldn’t we go and say “I’ll work on something” and then we get it out there in the doing part, I’m going to get it out there and then I’m going to renew then I’m going to think about it and then do it again. Why wouldn’t we apply the same thing to our personal and professional lives? That’s the part that confuses me and that’s why this book series, I had to do it. I’ve seen so many of my colleagues and friends burn themselves out. I see too many people say “I crush it every day”, you’re not going to crush it every day.

PW: True.

DB: You could have the goal of crushing it every day, that’s fine. But you also have to have a realism – it’s like being in school and saying “I’m going to get an A in every single class”. That’s a great aim to have. Good! Aim High! Do your thing! You might be a valedictorian – beautiful! But more likely you’re going to have some B’s in there, you might even have some C’s.

PW: Oh, to bring back the memories Damon! My father yelling at me is so clear in my ear, please don’t do it to me. I just – I’ve had many therapist talk to me… No. I’m joking around [Chuckles].

DB: Okay. Alright.

PW: Totally joking! What inspires you today? I mean you are so clear on who you are and what you’re doing which is inspiring to me. But what inspires you?

DB: That’s a really good question. I think there’s quite a few things but the main thing is making a positive impact based on the tools that I have. I think there’s a couple layers to it. I’ll try not to get too, too deep.

PW: No. No. Go ahead.

DB: When I was, younger and being an African-American boy of the seventies, that was very much you making, or me I should say, me making a social impact. Like what are you going to contribute to his world? And I thought that I had to be a politician or a lawyer which I still love law. But a politician or a lawyer or something like that, I really liked art and creativity and obviously, technology which had a much smaller world when I was younger. I love all those things. But people in general don’t talk about artists making a revolutionary impact, and the ones that do, you can count them on one or two hands, people that say “Oh yeah. this person made a revolutionary impact” – but it’s pretty rare. And so, what I learned – and I’m sure some mentors told me then including my parents – was that you should be the very best you you can be and you doing, pursuing again your passion and being persistent about it and using your skills to the maximum, your talent, your creativity, your curiosity to the maximum, that in itself is making an impact. Not only as far as direct impact with, in my case, the books that I write and stuff like that. I appreciate the compliments you gave me earlier as far as impacting you and other folks, but also the indirect impact of showing the same thing that I was talking about with my son where me being able to express to him that I was being up super early in the morning because not only did I prioritize spending time with you during your first year but also I want to make sure that I made an impact on other people too and that required me sacrificing some things. And they were both important to me so I did what I had to do to make that happen. So, it’s not just a direct impact of things, as far as what we create and what we do. But also, a representation of something so that being a representation of me being the best Damon Brown that I can be. That in itself might inspire other people to be the best they can be too. And so, I think that kind of the core of the passion where it’s like let me do what I do to the maximum and that’s being as great of a father as I can be, that’s being as excellent of an author as I can be, that’s being as creative of and entrepreneur as I can be. There’s a new book out called Unmistakable by Srinivas Rao and I was on his podcast, the Unmistakable Creative about two or three years ago talking about “Our Virtual Shadow”. And that was right before he blew up, so I felt kind of a kin to him, something like “Oh man I was on your podcast when it was smaller and now its huge!”. But he has a new book that just came out a couple of months ago called Unmistakable and the artist that he used is, who also did the cover of the book, his name is Mars Dorian I think. So, its Mars like the planet and I believe its D-O-R-I-A-N. He has this amazing quote for Mars Dorian, he says “I want my art to be so distinctive I don’t need to put my name on it”. Even today, I heard that quote from Srini months ago and it still gives me chills. That’s the mission, that the passion right there. Anyone who knows me and then say Cuddlr would say “That’s something that Damon would co-found”. Anyone who knows me and then read “Our Virtual Shadow” says “Oh yeah I get it”. Anyone who reads Porn & Pong and then meets me says “Oh! I see it”. No one can duplicate that. And so, that’s what I mean by fulfilling that passion with persistence, with purpose. Once those things are together and you have that core together, you can’t be duplicated. One quick anecdote. Porn & Pong when it came out, that was my biggest book at that time and so that’s what I was most known for and about a year and a half later, coz I went on book tour – and that’s a whole different story, but that was another bootstrapped effort coz I put myself across the country, lots of crowd, lots of couch or anything. But that was a lot of fun and that was an early test run for entrepreneurship but I didn’t realize it at that time. Anyway, the book came out in 2008. Around 2010, so a little bit after the book came out, I was trying to get involved with other projects, I got a random tweet and I was really into Twitter at that time, I still am but that was kind of at my peak at that time. And there was a random tweet from a stranger and he said “Hey Damon! I think someone just rewrote your book and just put it into an article”. And I was like “What? It doesn’t make any sense”. And they give the link and then they also tagged the other person. I was like “Woah! What is going on here?”. And so, I click on it and sure enough, a person had taken I think it was like the first chapter or one of the chapters from the book, changed a couple of words and then just put it in there.

PW: [Laughs]

DB: I bring that up not from a sense of bitterness coz that’s kind of the age we’re in. And the guy, he had taken it down, I can’t really remember what happened it was several years ago. But it ends up getting resolved. But my point is that, is that I didn’t have to worry about someone taking my stuff. I didn’t have to worry about watching my back and making sure that everything was secure. I have people that identify with my work so strongly, they’re going to tell me when other people are taking it.

PW: Wow! That’s good. That’s totally cool, Yeah.

DB: It’s like the proverbial horizon man where I got people behind, I have a bunch of people behind me. Like…

PW: Although Sprint now has taken that guy [Laughs]

DB: [Laughs] Now I’m baiting myself.

PW: [Laughs]

DB: He will always be at the horizon. I don’t know…

PW: [Laughs] He will. He will. He’s just running after money right now.

DB: I hope they pay him well. Coz I think that’s the only money he’s getting when it comes to that. If he’s going to do that as spokesman, your word is your bond.

PW: No one’s going to trust you again. He better…

DB: Exactly! My whole point is that there’s so many reasons why you should know what your purpose is. And then once you know what your purpose is and you push it as hard as you can, then you don’t have to worry about people stealing your thunder because they can’t. They can’t! No one else can be another Damon, it’s not possible. Even if someone else tried to write Porn & Pong or the Bite-sized Entrepreneur series or whatever, no one’s experienced what I experienced and that’s one of the reasons why I try to do a level of honesty in the series. And now it all started with the Inc column where I was putting it all out there. I have one Inc column called the Emotional Skills Necessary to Sell Your Company. And it’s just a short, honest, 500-word piece about what it was like to sell Cuddlr and the emotional intelligence necessary to get through it. Because we have this idealized thing where it’s like “I’m going to create something, I’m going to break my back on it, and then I’m going to sell it right away”. And it’s like “no, there’s a loss, there’s a bitter sweetness there that needs to be processed”. And as much as I talk about emotional intelligence and read books on emotional intelligence and try to practice high emotional intelligence, when we sold the company it was like going – the popular saying today is like “going zero to hundred”.

PW: Real-quick.

DB: Real-quick, yeah, exactly. Recently I saw someone saying the opposite. That’s like a 100 to 0 real quick. And that’s exactly what it was like. It was like suddenly stepping on the brakes and if you don’t have your stuff together, you go on through the windshield. And so, I talk about that in the column but there’s a high level – ideally a high level, at least with my standard – of honesty that I try to have with the book series to say that there’s no such thing as a perfect entrepreneur. You’re going to have bad days. You’re not meant to be productive every single day. At certain times, if you’re tired or you have to procrastinate, you’re not having a mental breakthrough right now then maybe your mind needs to process something. And then that’ll make the ideas stronger when you come back to it the next day. There’s so much pressure we put on ourselves to be perfect, to go ahead and crush it every day. To go ahead and say I’m going to start this company, it’s going to go wild and then it’s going to get sold. I think that kind of goes back to something we talked about earlier where if you end up starting something that you think is going to get acquired, if start something and you think it’s going to be worth a billion dollars, how long are you going to be patient?

PW: Uh-huh.

DB: Do you understand? What’s going to happen when that first sign that it might not work, what are you going to do then? What are you going to do then? You got to make sure you know why you’re doing it. If we were trying create Cuddlr to get acquired, to make a little bit of money, Cuddlr would have a totally different product – I’d tell you that.

PW: Damon, I could talk to you for a day and more. I mean you are probably for me, and I’ve said this offline and I’ll say it online, probably one of my most inspiring guest that I’ve have.

DB: Wow. Thank you.

PW: Just because of so many diverse things that you talk about and I’m totally about intimacy and tech because I think in some strange, odd way, we’d become a much more social society online but we’re introverts in so many aspects and its robbed us of genuine, true human interaction and I love people that delve into the psychology of intimacy and tech and how to still remain human. Well you do this and you build businesses and I would highly suggest to people that are listening to this to go out and look at TEDxJackson and his TED speech about the positive power of observation. All of the different topics and content that you create Damon is amazing like the example, or not the example but the real-life situation where you talked about writing for Playboy and Family Circle. The diversity in your writing and the content that you put out is so true to form to your point. There’s not a lot of people that talk about intimacy and tech and I could see your writing without you even putting “by Damon Brown” in there anywhere. And this has just been amazing for me, the conversations that we’ve had and I love all of the insight that you’ve given. Before we close here can you share anything the you’re working on now or I know we have the upcoming book the Productive Bite-Sized Entrepreneur which will be released on Amazon on the 26th, is there anything else that you’d like to share if somebody wants to get in contact with you or read some of your other writings, how can they do that? What would you like to share with us?

DB: So, the main hub is damonbrown.net. I’m so very active on Twitter and that’s @browndamon, B-R-O-W-N-D-A-M-O-N, ditto for Facebook coz I have a Facebook page as well. There’s a few things that I’m doing that are interesting and they’re kind of on the horizon and I can’t quite talk about them yet. And so right now the focus is really on the Bite-Sized Entrepreneur series and it’s a lot of stuff that I want to pass on to other people who believe that because they have other things to take care about in their life, that they have some type of restrictions as far as what they do – as my son speaks in the background. [Laughs]

PW: [Laughs]

DB: That’s about it. So, that’s a really big part of it. One of the things that I’m doing with the Bite-Sized Entrepreneur series is looking at the different ways that we can have a grabbable, actionable traits, a skill-set, a toolbox. People who aren’t quite entrepreneurs yet can grab it and they can prepare themselves coz you really have to get prepared. You have to kind of get in the right mindset. And so, what I’m doing is taking that and putting it into as many different ways as possible – let’s spread the message. So, the Original Bite-Sized Entrepreneur – that’s available on Kindle, that’s available on paperback, that’s available on audio book [Laughs]. I’m sorry my son wants pancakes. [Laughs] So, the Bite-Sized Entrepreneur is available on audiobook, on Kindle, on paperback. I also do talks related to the Bite-Sized Entrepreneur through something called Geniecast and Geniecast actually allows you to do virtual speaking engagements. And so, if you like my TED talks, then I can actually come and speak to your organization and go from there. And it’s truly a virtual medium which is totally amazing and different. And then finally I have a class on Teachable and that’s taking the core ideas of the Bite-Sized Entrepreneur and putting into a more interactive medium. And so, I spent a little bit of time as Adjunct Professor a couple of years ago with JFK University up at the Bay Area. I’ve done a lot of lecturing so teaching is kind of very much a part of my thing. You’ll probably get some of the ideas in the Bite-Sized Entrepreneur series and so the Teachable class does that as well. And that’s a paylancing.teachable.com, so P-A-Y-L-A-N-C-I-N-G. and so those are the big things I’m working on and definitely keep an eye in the space coz there will be some other books that will be coming out that will hopefully help some people move forward in their entrepreneurship.

PW: Damon, this had been wonderful in every way. I really appreciate the time you’ve taken out with us.

DB: Yeah, thank you. Thank you so much having me and we’ll have to catch up in person soon.

PW: We will. We will indeed. Thanks, a lot.

DB: Thanks, Priest. Goodbye.

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